I'm not sure who first had the idea of pairing red wine and chocolate together, but it's gotten out of hand. For once and for all, let me say it loud and clear: dry red wine and chocolate do not go together.
Why would someone lie to you and try to convince you that this is something you should enjoy? Why would the powers that be—the red-wine pushers and the chocolate coercers—set you up for such flavor failure, particularly around Valentine's Day when presumably you want to impress the object of your affections? I don't know. But I'm here to help.
Here's why the combination of red wine and chocolate is never going to truly taste good. Sugar. A sip of dry red wine without any perceptible sweetness will turn bitter and sour when taken with sweetened chocolate. Unless you're munching on plain roasted cocoa nibs, back away from the Cabernet, please.
Pairing wine and chocolate isn't hard, though—look for a wine with some sweetness, and the whole thing can come together beautifully. Don't let the word "sweetness" or the phrase "dessert wine" scare you away. We're not talking about wine coolers here. A proper dessert wine, when paired with a sweet food, will taste less sweet than it might on its own. Think of the wine as the raspberry syrup drizzled across your molten chocolate cake: it adds the contrasting flavor to make the chocolate pop.
The first step: identify your chocolate. Are you 80% cocoa kind of person or do you have a thing for milk chocolate mousse? Again, sugar is what we're talking about. The darker the chocolate, the less sweet it is, and the less sweet the wine needs to be for a perfect pairing. Do you make delicious chocolate pudding with cups of sugar in it? That's going to call for a sweeter wine.
Also think about what is accompanying your chocolate. Are you enjoying a chocolate and berry tart? The fruit may add some bright acidity that will mute the sweetness of the dessert, so that you can select a less richly sweet wine. More into hazelnut? That may call for a less fruit-forward wine in favor of one with savory flavors.
Ok, you've got the theory. Let's get you set up with some specific recommendations.
Truffles and Bonbons
You've got to love chocolates nestled in a tacky red foil heart-shaped box...but you'll love them even more with something to sip alongside. This classic Valentine's Day gift calls for a young and bright dessert wine like a ruby port. These are babies compared to aged or oxidized ports, but a ruby is meant to be drunk when young. (Aren't we all?) The style offers bright red berry flavors and lovely sweetness with an extra alcoholic kick from the traditional addition of distilled spirit to the wine. The ruby port from Quinto do Infantado is a favorite of ours—and offers great value so you can splurge for a 36-piece truffle box.
Light and airy mousse (such as this one) deserves a more sprightly wine, perhaps something with bubbles. A Brachetto from Italy's Piedmont region is lightly sparkling and semi-sweet. Think of it as a red version of Moscato, but with more herbal and fresh-picked strawberry flavors. Brachetto is also a bit lower in alcohol, helping to ensure that you'll be awake for whatever comes after a romantic dinner. We like the well-balanced 'Birbet' from Cascina Ca 'Rossa, which has enough acidity to keep it from being cloying.
Molten Chocolate Cake
This gooey and intense dessert can handle a denser wine. The warmth of the cake's liquid center is well-matched by a fortified wine, and something aged will have added complexity that plays well with the richness of the cake. We continue to be obsessed with wines from Maury, a French region near the more famous Banyuls that makes fortified wines with a less hefty price tag. Maury wines are fortified (like port is) so that they have both higher alcohol and residual sugar. The reds are made from Grenache grapes, and are brooding enough for this serious dessert. The Mas Amiel 10 Ans d'Age reminded us of concentrated blackberries...with a touch of walnuts on the finish.
Have Fun With It!
Now that you have some ideas to get started with, get out there find some chocolate! Let us know in the comments: do you have a favorite wine to drink with chocolate? Are you into port with dessert? Ever tried Madeira? What about Brachetto?